EP2654699B1 - Active ingredient combinations of glyceryl glucosides and one or more preservatives - Google Patents
Active ingredient combinations of glyceryl glucosides and one or more preservatives Download PDFInfo
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- EP2654699B1 EP2654699B1 EP11788170.6A EP11788170A EP2654699B1 EP 2654699 B1 EP2654699 B1 EP 2654699B1 EP 11788170 A EP11788170 A EP 11788170A EP 2654699 B1 EP2654699 B1 EP 2654699B1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/60—Sugars; Derivatives thereof
- A61K8/602—Glycosides, e.g. rutin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/007—Preparations for dry skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/10—Washing or bathing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Definitions
- the present invention relates to drug combinations of glucosylglycerides and one or more preservatives and their use in the field of cosmetic and pharmaceutical dermatology.
- the present invention relates to active ingredients and cosmetic or dermatological preparations containing such drug combinations.
- the outermost layer of the epidermis, the stratum corneum (horny layer), is of particular importance as an important barrier layer, inter alia. for protection against environmental influences and dehydration.
- the horny layer is constantly worn in contact with the environment and must therefore be renewed continuously.
- a skin model widely used today in the art understands the stratum corneum as a two-component system, similar to a brick wall (brick-mortar model).
- the corneocytes horny cells
- the complex composite lipid membrane in the intercellular spaces corresponds to the mortar.
- the epidermal lipids In addition to their barrier effect against external chemical and physical influences, the epidermal lipids also contribute to the cohesion of the horny layer and have an influence on the skin smoothness. In contrast to the sebaceous gland lipids, which do not form a closed film on the skin, the epidermal lipids are distributed over the entire horny layer.
- N atural M oisturizing F actor NMF
- Cleaning means the removal of (environmental) dirt and thus causes an increase in mental and physical well-being.
- Cleaning the surface of the skin and hair is a very complex process, depending on many parameters.
- substances coming from outside such as, for example, hydrocarbons or inorganic pigments from a wide variety of environments as well as residues of cosmetics or undesired microorganisms should be removed as completely as possible.
- the body's excretions such as sweat, sebum, dandruff and hair dandruff are to be washed off without profound interventions in the physiological balance.
- the preservation of cosmetic preparations has a high demand, since on the one hand sufficient preservation must be ensured to protect the formulation from bacterial attack, on the other hand, negative effects of preservatives on the tolerability, stability and sensory properties of the formulation must be prevented.
- the preservatives must therefore be effective, toxicologically safe, well tolerated by the skin, stable formulatable and inexpensive to produce.
- preservatives such as formaldehyde scavengers, parabens, phenols and their derivatives, bisguanidines, and halogenated compounds
- preservatives such as formaldehyde scavengers, parabens, phenols and their derivatives, bisguanidines, and halogenated compounds
- Paraben-free preservatives e.g. Isothiazolinones, benzethonium chloride, piroctone olamine and lauroylethylarginate are used as preservatives. They have in common that they produce a slippery skin feel on the skin when diluted with water and have an unsatisfactory viscosity behavior at very low temperatures. Under these circumstances, such preparations can no longer be removed from the packaging.
- Cosmetic and dermatological preparations can be in various forms. For example, they may contain a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsion, for example water-type. in oil-in-water (W / O / W), a gel, a solid stick, an ointment or even an aerosol.
- W / O water-in-oil
- O / W oil-in-water
- the cosmetic preparation is stored in a bottle, squeeze bottle, pump spray or aerosol can and applied out of it.
- the preparation advantageously contains one or more anionic surfactants. These are according to the invention advantageously in a concentration of 1 to 20% by weight, and according to the invention preferably in a concentration of 5 to 12% by weight, in each case based on the total weight of the preparation, in the preparation. Particularly preferred according to the invention is the use of narium lauryl ether sulfate as anionic surfactant.
- the preparation advantageously contains one or more amphoteric surfactants. These are according to the invention advantageously in a concentration of 1 to 20% by weight, and according to the invention preferably in a concentration of 3 to 8% by weight, in each case based on the total weight of the preparation, in the preparation. Particularly preferred according to the invention is the use of cocamidopropylbetaine as the amphoteric surfactant.
- the preparation may advantageously also contain nonionic surfactants.
- nonionic surfactants particularly preferred according to the invention is the use of PEG-7 glyceryl cocoate and / or PEG-40 hydrogenated castor oil as nonionic surfactant.
- cationic polymer or mixtures of cationic polymers in a concentration of 0.01 to 2% by weight, preferably in a concentration of 0.05 to 1.5% by weight and particularly preferably from 0.1 to 1.0% by weight, each based on the total weight the preparation to use.
- compositions optionally contain, in addition to the aforementioned substances, the additives customary in cosmetics, for example perfumes, dyes, antimicrobials, moisturizing agents, complexing and sequestering agents, pearlescing agents, plant extracts, vitamins, active ingredients, preservatives, bactericides, pigments which have a coloring effect , Thickening, softening, moisturizing and / or moisturizing substances, or other conventional ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
- the additives customary in cosmetics, for example perfumes, dyes, antimicrobials, moisturizing agents, complexing and sequestering agents, pearlescing agents, plant extracts, vitamins, active ingredients, preservatives, bactericides, pigments which have a coloring effect , Thickening, softening, moisturizing and / or moisturizing substances, or other conventional ingredients of a cosmetic or dermatological formulation such as alcohol
- inventively advantageous usable active ingredients, auxiliaries and additives are by no means limited to the substances and compounds mentioned here by name.
- skin-care fat or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol
- skin-care fat or fat-like substances such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol
- customary cosmetic excipients for preparing the deodorizing preparations according to the inventive use in the proportions customary for such preparations as well as slime-forming substances and thickeners, for example hydroxyethyl or hydroxypropylcellulose, polyacrylic acid, polyvinylpyrrolidone, but also in small quantities cyclic silicone oils (polydimethylsiloxanes) as well as liquid polymethylphenylsiloxanes of low viscosity.
- antioxidants it is also advantageous to add conventional antioxidants to the preparations. As favorable antioxidants, it is possible to use all antioxidants which are suitable or customary for cosmetic and / or dermatological applications.
- the amount of antioxidants (one or more compounds) in the preparations is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20% by weight, in particular from 1 to 10% by weight, based on the total weight of the preparation ,
- Suitable propellants for sprayable from aerosol containers cosmetic and / or dermatological preparations are the usual known volatile, liquefied propellants, such as hydrocarbons (propane, butane, isobutane) suitable, which can be used alone or in mixture with each other. Also, compressed air is advantageous to use.
- Cosmetic preparations may also be present as gels which, in addition to an effective content of the active ingredient according to the invention and solvents used for this purpose, preferably water, also organic thickening agents, e.g. Gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, e.g. For example, aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate.
- the thickener is present in the gel e.g. in an amount of between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
- phase A The ingredients of phase A are mixed together until a homogeneous phase is obtained.
- Ucare Polymer JR 400 is interspersed in the water of phase B.
- the phase B is heated with stirring to about 70 ° C until a clear solution is formed.
- Phase B is cooled and added to Phase A.
- phase C The water of phase C is mixed with the sodium hydroxide solution.
- Jaguar Excel is slowly sprinkled while stirring. Subsequently, the mixture is heated to 70 ° C and stirred until a homogeneous phase is formed. With stirring, the citric acid is added. Phase C is cooled and added to phase A.
- Eumulgin HRE 40 is melted at a temperature of about 40 ° C.
- the remaining phase D raw materials are added to the Eumulgin HRE 40.
- the phase is mixed homogeneously and added to phase A.
- phase E The addition of the ingredients of phase E is carried out in the order given. It is stirred until a homogeneous shampoo is formed.
- phase A The ingredients of phase A are mixed until a homogeneous mixture is obtained.
- Eumulgin HRE 40 is melted at a temperature of about 40 ° C.
- the remaining Phase B raw materials are added to the Eumulgin HRE 40.
- the phase is mixed homogeneously and added to phase A.
- Glycerylsteratcitrat 1.0 1.5 1.5 0.5 0.25 Cetylstearylalkohol 2.5 5 0.5 2.0 1.5 ethylhexylmethoxycinnamate 5.0 3.0 2.0 2.0 5.0 Ethylhexylglycerin 1 --- 0.5 1 --- aluminum chlorohydrate --- 1 0.02 1 --- ethanol --- --- 3.0 1 - Ammonium acryloyldimethyltairate / VP copolymer 0.5 0.75 0.5 2.0 0.25 Blue, water-soluble dye (Blue No.
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- Medicinal Chemistry (AREA)
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Description
Die vorliegende Erfindung betrifft Wirkstoffkombinationen aus Glucosylglyceriden und einem oder mehreren Konservierungsmitteln sowie deren Verwendung auf dem Gebiete der kosmetischen sowie der pharmazeutischen Dermatologie.The present invention relates to drug combinations of glucosylglycerides and one or more preservatives and their use in the field of cosmetic and pharmaceutical dermatology.
Insbesondere betrifft die vorliegende Erfindung Wirkstoffe und kosmetische oder dermatologische Zubereitungen, solche Wirkstoffkombinationen enthaltend.In particular, the present invention relates to active ingredients and cosmetic or dermatological preparations containing such drug combinations.
Die äußerste Schicht der Epidermis, das Stratum corneum (Hornschicht), ist als wichtige Barriereschicht von besonderer Bedeutung u.a. für den Schutz vor Umwelteinflüssen und Austrocknung. Die Hornschicht wird im Kontakt mit der Umwelt ständig abgenutzt und muß deshalb ununterbrochen erneuert werden.The outermost layer of the epidermis, the stratum corneum (horny layer), is of particular importance as an important barrier layer, inter alia. for protection against environmental influences and dehydration. The horny layer is constantly worn in contact with the environment and must therefore be renewed continuously.
Ein heute in der Fachwelt weitverbreitetes Hautmodell faßt das Stratum corneum als Zwei-Komponenten-System, ähnlich einer Ziegelsteinmauer (Ziegelstein-Mörtel-Modell), auf. In diesem Modell entsprechen die Korneozyten (Hornzellen) den Ziegelsteinen, die kompliziert zusammengesetzte Lipidmembran in den Interzellularräumen entspricht dem Mörtel.A skin model widely used today in the art understands the stratum corneum as a two-component system, similar to a brick wall (brick-mortar model). In this model, the corneocytes (horny cells) correspond to the bricks, the complex composite lipid membrane in the intercellular spaces corresponds to the mortar.
Außer ihrer Barrierewirkung gegen externe chemische und physikalische Einflüsse tragen die epidermalen Lipide auch zum Zusammenhalt der Hornschicht bei und haben Einfluß auf die Hautglätte. Im Gegensatz zu den Talgdrüsenlipiden, die keinen geschlossenen Film auf der Haut ausbilden, sind die epidermalen Lipide über die gesamte Hornschicht verteilt.In addition to their barrier effect against external chemical and physical influences, the epidermal lipids also contribute to the cohesion of the horny layer and have an influence on the skin smoothness. In contrast to the sebaceous gland lipids, which do not form a closed film on the skin, the epidermal lipids are distributed over the entire horny layer.
Das äußerst komplexe Zusammenwirken der feuchtigkeitsbindenden Substanzen und der Lipide der oberen Hautschichten ist für die Regulation der Hautfeuchte sehr wichtig. Daher enthalten Kosmetika in der Regel, neben ausgewogenen Lipidabmischungen und Wasser, wasserbindende Substanzen. Hierzu zählen u.a. Polyole wie Glycerin, Sorbit und Xylit, ethoxylierte Polyole sowie hydrolysierte Proteine. Weitere Anwendung finden die im natürlichen Feuchthaltefaktor (sogenannter Natural Moisturizing Factor = NMF) enthaltenen Substanzen, wie z.B. Harnstoff, Kohlenhydrate (z. B. Glucose) und Aminosäuren (z. B. Serin). Diese Substanzen sind daher für die Pflegeleistung eines kosmetischen Produktes von besonderer Bedeutung, insbesondere auch aufgrund ihrer relativ guten Haut- und Schleimhautverträglichkeit.The extremely complex interaction of the moisture-binding substances and the lipids of the upper skin layers is very important for the regulation of skin moisture. Therefore, cosmetics usually contain, in addition to balanced lipid mixtures and water, water-binding substances. These include polyols such as glycerin, sorbitol and xylitol, ethoxylated polyols and hydrolyzed proteins. Further application find in the natural moisturizing factor (so-called N atural M oisturizing F actor = NMF) contained substances such as urea, carbohydrates (eg., glucose) and amino acids (eg., serine). These substances are therefore of particular importance for the care performance of a cosmetic product, in particular because of their relatively good skin and mucous membrane compatibility.
Der Wunsch nach sauberer Haut ist wohl so alt wie die Menschheit, denn Schmutz, Schweiß und Reste abgestorbener Hautpartikel bieten den idealen Nährboden für Krankheitserreger und Parasiten aller Art. Die Lust an der Körperhygiene wurde stetig verstärkt, als in den 60er Jahren des 20. Jahrhunderts neben der "klassischen" Seife auch flüssige Reinigungsmittel mit neu entwickelten synthetischen Tensiden formuliert werden konnten. Baden und Duschen sind seitdem aus unserem täglichen Leben nicht mehr wegzudenken. Den Verbrauchern stehen heutzutage eine Vielzahl von Produkten für die Reinigung der verschiedenen Körperpartien zur Verfügung.The desire for clean skin is probably as old as humanity, because dirt, sweat and remains of dead skin particles provide the ideal breeding ground for pathogens and parasites of all kinds. The desire for personal hygiene was steadily increased, as in the 60s of the 20th century In addition to the "classic" soap and liquid detergents could be formulated with newly developed synthetic surfactants. Since then, bathing and showering have become indispensable in our daily lives. Consumers today have a variety of products available for cleaning the various body parts.
Reinigung bedeutet das Entfernen von (Umwelt-) Schmutz und bewirkt damit eine Erhöhung des psychischen und physischen Wohlbefindens. Die Reinigung der Oberfläche von Haut und Haaren ist ein sehr komplexer, von vielen Parametern abhängiger Vorgang. Zum einen sollen von außen kommende Substanzen wie beispielsweise Kohlenwasserstoffe oder anorganische Pigmente aus unterschiedlichsten Umfeldern sowie Rückstände von Kosmetika oder auch unerwünschte Mikroorganismen möglichst vollständig entfernt werden. Zum anderen sind körpereigene Ausscheidungen wie Schweiß, Sebum, Haut- und Haarschuppen ohne tiefgreifende Eingriffe in das physiologische Gleichgewicht abzuwaschen.Cleaning means the removal of (environmental) dirt and thus causes an increase in mental and physical well-being. Cleaning the surface of the skin and hair is a very complex process, depending on many parameters. On the one hand, substances coming from outside such as, for example, hydrocarbons or inorganic pigments from a wide variety of environments as well as residues of cosmetics or undesired microorganisms should be removed as completely as possible. On the other hand, the body's excretions such as sweat, sebum, dandruff and hair dandruff are to be washed off without profound interventions in the physiological balance.
An die Konservierung kosmetischer Zubereitungen wird ein hoher Anspruch gestellt, da einerseits eine ausreichende Konservierung zum Schutz der Formulierung vor bakteriellem Befall gewährleistet sein muss, andererseits negative Einflüsse der Konservierungsmittel auf die Verträglichkeit, Stabilität und sensorischen Eigenschaften der Formulierung verhindert werden müssen. Die Konservierungsmittel müssen demnach wirksam, toxikologisch unbedenklich, gut hautverträglich, stabil formulierbar sowie preiswert herstellbar sein.The preservation of cosmetic preparations has a high demand, since on the one hand sufficient preservation must be ensured to protect the formulation from bacterial attack, on the other hand, negative effects of preservatives on the tolerability, stability and sensory properties of the formulation must be prevented. The preservatives must therefore be effective, toxicologically safe, well tolerated by the skin, stable formulatable and inexpensive to produce.
Eine Vielzahl an Konservierungsmitteln, wie Formaldehydabspalter, Parabene, Phenole- und deren Derivate, Bisguanidine und halogenierte Verbindungen, haben zwar eine hohe antimikrobielle Wirksamkeit, können aber Hautirritationen und allergische Reaktionen verursachen und werden daher von Verbrauchern kritisch betrachtet und überwiegend als unerwünscht angesehen.While a variety of preservatives, such as formaldehyde scavengers, parabens, phenols and their derivatives, bisguanidines, and halogenated compounds, have high antimicrobial efficacy, they can cause skin irritation and allergic reactions, and are therefore viewed critically by consumers and are believed to be undesirable.
Parabenfreie Konservierungsmittel, wie z.B. Isothiazolinone, Benzethoniumchlorid, Piroctonolamin und Lauroylethylarginat werden als Konservierungsmittel eingesetzt. Ihnen ist gemeinsam, dass sie auf der Haut bei der Verdünnung mit Wasser ein glitschiges Hautgefühl erzeugen und ein unbefriedigendes Viskositätsverhalten bei sehr niedrigen Temperaturen aufweisen. Unter diesen Umständen lassen sich derartige Zubereitungen nicht mehr der Verpackung entnehmen.Paraben-free preservatives, e.g. Isothiazolinones, benzethonium chloride, piroctone olamine and lauroylethylarginate are used as preservatives. They have in common that they produce a slippery skin feel on the skin when diluted with water and have an unsatisfactory viscosity behavior at very low temperatures. Under these circumstances, such preparations can no longer be removed from the packaging.
Es besteht daher der Bedarf an Zubereitungen, die die Nachteile des Standes der Technik beheben.There is therefore a need for preparations which overcome the disadvantages of the prior art.
Es war nach all diesem überraschend und nicht vorhersehbar, daß die Verwendung kosmetischer Zubereitungen, umfassend eine Wasser und/oder Ölphase sowie ferner Wirkstoffkombinationen aus
- (i) einem oder mehreren Konservierungsmitteln gewählt aus der Gruppe der Isothiazolinone, Benzethoniumchlorid, Piroctonolamin und Lauroylethylarginat
und. - (ii) einem oder mehreren Glucosylglyceriden gewählt aus der Gruppe der der allgemeinen Formel
- (iii) eine Substanz, gewählt aus der Gruppe der anionischen, nichtionischen bzw. amphoteren Tenside und der kationischen Polymere
als Reinigungsmittel,
die Nachteile des Standes der Technik beseitigen.
- (I) one or more preservatives selected from the group of isothiazolinones, benzethonium chloride, Piroctonolamin and lauroylethylarginate
and. - (ii) one or more glucosylglycerides selected from the group of the general formula
- (iii) a substance selected from the group of anionic, nonionic or amphoteric surfactants and the cationic polymers
as a cleaning agent,
eliminate the disadvantages of the prior art.
Dabei wird die Zubereitung bevorzugt als Duschgel, Schaum- und Wannenbad, Shampoo und/oder Gesichtsreiniger verwendet. Kosmetische und dermatologische Zubereitungen können in verschiedenen Formen vorliegen. So können sie z.B. eine Lösung, eine wasserfreie Zubereitung, eine Emulsion oder Mikroemulsion vom Typ Wasser-in-Öl (W/O) oder vom Typ Öl-in-Wasser (O/W), eine multiple Emulsionen, beispielsweise vom Typ Wasser-in-Öl-in-Wasser (W/O/W), ein Gel, einen festen Stift, eine Salbe oder auch ein Aerosol darstellen.The preparation is preferably used as a shower gel, foam and bath tub, shampoo and / or facial cleanser. Cosmetic and dermatological preparations can be in various forms. For example, they may contain a solution, an anhydrous preparation, an emulsion or microemulsion of the water-in-oil (W / O) type or of the oil-in-water (O / W) type, a multiple emulsion, for example water-type. in oil-in-water (W / O / W), a gel, a solid stick, an ointment or even an aerosol.
Es ist erfindungsgemäß vorteilhaft, wenn die kosmetische Zubereitung in einer Flasche, Quetschflasche, Pumpspray-, oder Aerosoldose aufbewahrt und aus dieser heraus angewendet werden.It is advantageous according to the invention if the cosmetic preparation is stored in a bottle, squeeze bottle, pump spray or aerosol can and applied out of it.
Die Zubereitung enthält vorteilhaft ein oder mehrere anionische Tenside. Diese liegen erfindungsgemäß vorteilhaft in einer Konzentration von 1 bis 20 Gewichts-%, und erfindungsgemäß bevorzugt in einer Konzentration von 5 bis 12 Gewichts-%, jeweils bezogen auf das Gesamtgewicht der Zubereitung, in der Zubereitung vor. Erfindungsgemäß besonders bevorzugt ist dabei der Einsatz von Nariumlaurylethersulfat als anionischem Tensid. Die Zubereitung enthält vorteilhaft ein oder mehrere amphotere Tenside. Diese liegen erfindungsgemäß vorteilhaft in einer Konzentration von 1 bis 20 Gewichts-%, und erfindungsgemäß bevorzugt in einer Konzentration von 3 bis 8 Gewichts-%, jeweils bezogen auf das Gesamtgewicht der Zubereitung, in der Zubereitung vor. Erfindungsgemäß besonders bevorzugt ist dabei der Einsatz von Cocamidopropylbetain als amphoterem Tensid.The preparation advantageously contains one or more anionic surfactants. These are according to the invention advantageously in a concentration of 1 to 20% by weight, and according to the invention preferably in a concentration of 5 to 12% by weight, in each case based on the total weight of the preparation, in the preparation. Particularly preferred according to the invention is the use of narium lauryl ether sulfate as anionic surfactant. The preparation advantageously contains one or more amphoteric surfactants. These are according to the invention advantageously in a concentration of 1 to 20% by weight, and according to the invention preferably in a concentration of 3 to 8% by weight, in each case based on the total weight of the preparation, in the preparation. Particularly preferred according to the invention is the use of cocamidopropylbetaine as the amphoteric surfactant.
Darüber hinaus kann die Zubereitung in vorteilhafter Weise auch nichtionische Tenside enthalten. Erfindungsgemäß besonders bevorzugt ist dabei der Einsatz von PEG-7 Glycerylcocoat und/oder PEG-40 hydriertem Rizinusöl als nichtionischem Tensid.In addition, the preparation may advantageously also contain nonionic surfactants. Particularly preferred according to the invention is the use of PEG-7 glyceryl cocoate and / or PEG-40 hydrogenated castor oil as nonionic surfactant.
Es ist ebenfalls vorteilhaft, den Zubereitungen im Sinne der vorliegenden Erfindung kationische Polymere zuzufügen. Geeignete kationische Polymere sind beispielsweise
- quaternisierte Cellulose-Derivate, wie z.B. Polyquaternium-10, wie sie unter den Bezeichnungen Celquat und Polymer JR im Handel erhältlich sind
- kationische Guar-Derivate, wie insbesondere die unter den Handelsnamen Cosmedia Guar und Jaguar vertriebenen Produkte
- polymere Dimethyldiallylammoniumsalze und deren Copolymere mit Estern und Amiden von Acrylsäure und Methacrylsäure, wie insbesondere die unter
den Bezeichnungen Merquat 100 und Merquat 550 im Handel erhältlichen Produkte.
- quaternized cellulose derivatives, such as Polyquaternium-10, as are commercially available under the names Celquat and Polymer JR
- cationic guar derivatives, such as in particular the products sold under the trade names Cosmedia Guar and Jaguar
- polymeric dimethyldiallylammonium salts and their copolymers with esters and amides of acrylic acid and methacrylic acid, in particular the products sold under the names Merquat 100 and Merquat 550 commercially available.
Vorteilhaft ist es insbesondere, kationisches Polymer oder Mischungen aus kationischen Polymeren in einer Konzentration von 0.01 bis 2 Gewichts-%, bevorzugt in einer Konzentration von 0.05 bis 1.5 Gewichts-% und besonders bevorzugt von 0.1 bis 1.0 Gewichts-%, jeweils bezogen auf das Gesamtgewicht der Zubereitung, einzusetzen.It is particularly advantageous, cationic polymer or mixtures of cationic polymers in a concentration of 0.01 to 2% by weight, preferably in a concentration of 0.05 to 1.5% by weight and particularly preferably from 0.1 to 1.0% by weight, each based on the total weight the preparation to use.
Die Zusammensetzungen enthalten außer den vorgenannten Substanzen gegebenenfalls die in der Kosmetik üblichen Zusatzstoffe, beispielsweise Parfüm, Farbstoffe, antimikrobielle Stoffe, rückfettende Agentien, Komplexierungs- und Sequestrierungsagentien, Perlglanzagentien, Pflanzenextrakte, Vitamine, Wirkstoffe, Konservierungsmittel, Bakterizide, Pigmente, die eine färbende Wirkung haben, Verdickungsmittel, weichmachende, anfeuchtende und/oder feuchthaltende Substanzen, oder andere übliche Bestandteile einer kosmetischen oder dermatologischen Formulierung wie Alkohole, Polyole, Polymere, Schaumstabilisatoren, Elektrolyte, organische Lösemittel oder Silikonderivate.The compositions optionally contain, in addition to the aforementioned substances, the additives customary in cosmetics, for example perfumes, dyes, antimicrobials, moisturizing agents, complexing and sequestering agents, pearlescing agents, plant extracts, vitamins, active ingredients, preservatives, bactericides, pigments which have a coloring effect , Thickening, softening, moisturizing and / or moisturizing substances, or other conventional ingredients of a cosmetic or dermatological formulation such as alcohols, polyols, polymers, foam stabilizers, electrolytes, organic solvents or silicone derivatives.
Die erfindungsgemäß vorteilhaften einsetzbaren Wirk-, Hilfs- und Zusatzstoffe sind dabei keineswegs auf die hier namentlich erwähnten Stoffe und Verbindungen beschränkt.The inventively advantageous usable active ingredients, auxiliaries and additives are by no means limited to the substances and compounds mentioned here by name.
Als übliche kosmetische Trägerstoffe zur Herstellung der desodorierenden Zubereitungen gemäß der erfindungsgemäßen Verwendung können neben Wasser, Ethanol und Isopropanol, Glycerin und Propylenglykol hautpflegende Fett- oder fettähnliche Stoffe, wie Ölsäuredecylester, Cetylalkohol, Cetylstearylalkohol und 2-Octyldodecanol, in den für solche Präparate üblichen Mengenverhältnissen eingesetzt werden sowie schleimbildende Stoffe und Verdickungsmittel, z.B. Hydroxyethyl- oder Hydroxypropylcellulose, Polyacrylsäure, Polyvinylpyrrolidon, daneben aber auch in kleinen Mengen cyclische Silikonöle (Polydimethylsiloxane) sowie flüssige Polymethylphenylsiloxane niedriger Viskosiät.In addition to water, ethanol and isopropanol, glycerol and propylene glycol, skin-care fat or fat-like substances, such as oleic acid decyl ester, cetyl alcohol, cetylstearyl alcohol and 2-octyldodecanol, can be used as customary cosmetic excipients for preparing the deodorizing preparations according to the inventive use in the proportions customary for such preparations as well as slime-forming substances and thickeners, for example hydroxyethyl or hydroxypropylcellulose, polyacrylic acid, polyvinylpyrrolidone, but also in small quantities cyclic silicone oils (polydimethylsiloxanes) as well as liquid polymethylphenylsiloxanes of low viscosity.
Es ist ebenfalls vorteilhaft, den Zubereitungen übliche Antioxidantien zuzufügen. Es können als günstige Antioxidantien alle für kosmetische und/oder dermatologische Anwendungen geeigneten oder gebräuchlichen Antioxidantien verwendet werden.It is also advantageous to add conventional antioxidants to the preparations. As favorable antioxidants, it is possible to use all antioxidants which are suitable or customary for cosmetic and / or dermatological applications.
Die Menge der Antioxidantien (eine oder mehrere Verbindungen) in den Zubereitungen beträgt vorzugsweise 0,001 bis 30 Gew.-%, besonders bevorzugt 0,05 - 20 Gew.-%, insbesondere 1 - 10 Gew.-%, bezogen auf das Gesamtgewicht der Zubereitung.The amount of antioxidants (one or more compounds) in the preparations is preferably from 0.001 to 30% by weight, particularly preferably from 0.05 to 20% by weight, in particular from 1 to 10% by weight, based on the total weight of the preparation ,
Sofern die kosmetische oder dermatologische Zubereitung eine Lösung oder Emulsion oder Dispersion darstellt, können als Lösungsmittel verwendet werden:
- Wasser oder wäßrige Lösungen
- Öle, wie Triglyceride der Caprin- oder der Caprylsäure, vorzugsweise aber Rizinusöl;
- Fette, Wachse und andere natürliche und synthetische Fettkörper, vorzugsweise Ester von Fettsäuren mit Alkoholen niedriger C-Zahl, z.B. mit Isopropanol, Propylenglykol oder Glycerin, oder Ester von Fettalkoholen mit Alkansäuren niedriger C-Zahl oder mit Fettsäuren;
- Alkohole, Diole oder Polyole niedriger C-Zahl, sowie deren Ether, vorzugsweise Ethanol, Isopropanol, Propylenglykol, Glycerin, Ethylenglykol, Ethylenglykolmonoethyl- oder -monobutylether, Propylenglykolmonomethyl, -monoethyl- oder - monobutylether, Diethylenglykolmonomethyl- oder -monoethylether und analoge Produkte.
- Water or aqueous solutions
- Oils, such as triglycerides of capric or caprylic acid, but preferably castor oil;
- Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with lower C-number alcohols, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with lower C-number alkanoic acids or with fatty acids;
- Alcohols, diols or polyols of low C number, and their ethers, preferably ethanol, isopropanol, propylene glycol, glycerol, ethylene glycol, ethylene glycol monoethyl or monobutyl ether, propylene glycol monomethyl, monoethyl or monobutyl ether, diethylene glycol monomethyl or monoethyl ether and analogous products.
Als Treibmittel für aus Aerosolbehältern versprühbare kosmetische und/oder dermatologische Zubereitungen sind die üblichen bekannten leichtflüchtigen, verflüssigten Treibmittel, beispielsweise Kohlenwasserstoffe (Propan, Butan, Isobutan) geeignet, die allein oder in Mischung miteinander eingesetzt werden können. Auch Druckluft ist vorteilhaft zu verwenden.Suitable propellants for sprayable from aerosol containers cosmetic and / or dermatological preparations are the usual known volatile, liquefied propellants, such as hydrocarbons (propane, butane, isobutane) suitable, which can be used alone or in mixture with each other. Also, compressed air is advantageous to use.
Natürlich weiß der Fachmann, daß es an sich nichttoxische Treibgase gibt, die grundsätzlich für die Verwirklichung der vorliegenden Erfindung in Form von Aerosolpräparaten geeignet wären, auf die aber dennoch wegen bedenklicher Wirkung auf die Umwelt oder sonstiger Begleitumstände verzichtet werden sollte, insbesondere Fluorkohlenwasserstoffe und Fluorchlorkohlenwasserstoffe (FCKW).Of course, those skilled in the art will recognize that there are inherently nontoxic propellants which would be useful in the practice of the present invention in the form of aerosol preparations, but which should be avoided due to adverse environmental effects or other concomitant conditions, especially fluorocarbons and chlorofluorocarbons (US Pat. CFC).
Kosmetische Zubereitungen können auch als Gele vorliegen, die neben einem wirksamen Gehalt am erfindungsgemäßen Wirkstoff und dafür üblicherweise verwendeten Lösungsmitteln, bevorzugt Wasser, noch organische Verdickungsmittel, z.B. Gummiarabikum, Xanthangummi, Natriumalginat, Cellulose-Derivate, vorzugsweise Methylcellulose, Hydroxymethylcellulose, Hydroxyethylcellulose, Hydroxypropylcellulose, Hydroxypropylmethylcellulose oder anorganische Verdickungsmittel, z. B. Aluminiumsilikate wie beispielsweise Bentonite, oder ein Gemisch aus Polyethylenglykol und Polyethylenglykolstearat oder -distearat, enthalten. Das Verdickungsmittel ist in dem Gel z.B. in einer Menge zwischen 0,1 und 30 Gew.-%, bevorzugt zwischen 0,5 und 15 Gew.-%, enthalten.Cosmetic preparations may also be present as gels which, in addition to an effective content of the active ingredient according to the invention and solvents used for this purpose, preferably water, also organic thickening agents, e.g. Gum arabic, xanthan gum, sodium alginate, cellulose derivatives, preferably methylcellulose, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose or inorganic thickening agents, e.g. For example, aluminum silicates such as bentonites, or a mixture of polyethylene glycol and polyethylene glycol stearate or distearate. The thickener is present in the gel e.g. in an amount of between 0.1 and 30% by weight, preferably between 0.5 and 15% by weight.
Es folgen vorteilhafte Ausführungsbeispiele der vorliegenden Erfindung.Following are advantageous embodiments of the present invention.
Die Messungen wurden unter folgenden Bedingungen durchgeführt:
Shampoozubereitungen
alle Konzentrationsangaben in Gew.-%
** Menge variabel zur Einstellung eines pH-Wertes von 4,8 bis 5,8
all concentration data in% by weight
** Quantity variable to set a pH of 4.8 to 5.8
Die Inhaltsstoffe der Phase A werden miteinander vermischt, bis eine homogene Phase entsteht.The ingredients of phase A are mixed together until a homogeneous phase is obtained.
Ucare Polymer JR 400 wird in das Wasser der Phase B eingestreut. Die Phase B wird unter Rühren auf ca. 70°C erwärmt bis eine klare Lösung entsteht. Phase B wird gekühlt und zur Phase A gegeben.Ucare Polymer JR 400 is interspersed in the water of phase B. The phase B is heated with stirring to about 70 ° C until a clear solution is formed. Phase B is cooled and added to Phase A.
Das Wasser der Phase C wird mit der Natronlauge gemischt. Jaguar Excel wird unter Rühren langsam eingestreut. Anschließend wird die Mischung auf 70°C erwärmt und gerührt, bis eine homogene Phase entstanden ist. Unter Rühren wird die Zitronensäure zugegeben. Die Phase C wird abgekühlt und zur Phase A gegeben.The water of phase C is mixed with the sodium hydroxide solution. Jaguar Excel is slowly sprinkled while stirring. Subsequently, the mixture is heated to 70 ° C and stirred until a homogeneous phase is formed. With stirring, the citric acid is added. Phase C is cooled and added to phase A.
Eumulgin HRE 40 wird bei einer Temperatur von ca. 40°C aufgeschmolzen. Die übrigen Rohstoffe der Phase D werden zum Eumulgin HRE 40 gegeben. Die Phase wird homogen vermischt und zur Phase A gegeben.Eumulgin HRE 40 is melted at a temperature of about 40 ° C. The remaining phase D raw materials are added to the Eumulgin HRE 40. The phase is mixed homogeneously and added to phase A.
Die Zugabe der Inhaltsstoffe der Phase E erfolgt in der angegebenen Reihenfolge. Es wird gerührt bis ein homogenes Shampoo entsteht.The addition of the ingredients of phase E is carried out in the order given. It is stirred until a homogeneous shampoo is formed.
Duschgelzubereitungen
alle Konzentrationsangaben in Gew.-%
** Menge variabel zur Einstellung einer Viskosität im Bereich von 3000 - 5000 mPas (gemssen mit HAAKE viscotester VT02 mit Rotor 1)
all concentration data in% by weight
** Quantity variable for setting a viscosity in the range of 3000 - 5000 mPas (measured with HAAKE viscotester VT02 with rotor 1)
Die Inhaltsstoffe der Phase A werden vermischt, bis eine homogene Mischung entsteht.The ingredients of phase A are mixed until a homogeneous mixture is obtained.
Eumulgin HRE 40 wird bei einer Temperatur von ca. 40°C aufgeschmolzen. Die übrigen Rohstoffe der Phase B werden zum Eumulgin HRE 40 gegeben. Die Phase wird homogen vermischt und zur Phase A gegeben.Eumulgin HRE 40 is melted at a temperature of about 40 ° C. The remaining Phase B raw materials are added to the Eumulgin HRE 40. The phase is mixed homogeneously and added to phase A.
Die Zugabe der Inhaltsstoffe der Phase C erfolgt unter Rühren in der angegebenen Reihenfolge.The addition of the ingredients of phase C is carried out with stirring in the order given.
Claims (4)
- Use of cosmetic preparations comprising a water and/or oil phase and further active ingredient combinations of(i) one or more preservatives selected from the group of isothiazolinones, benzethonium chloride, piroctone olamine and ethyl lauroyl arginate and(ii) one or more glucosyl glycerides selected from the group of the general formula(iii) a substance selected from the group of anionic, non-ionic and amphoteric surfactants and cationic polymersas cleansing agents.
- Use according to Claim 1, characterized in that said preparations comprise anionic surfactants at concentrations of 1 to 20% by weight, preferably 5 to 12% by weight, based in each case on the total weight of the preparation.
- Use according to Claim 1, characterized in that said preparations comprise amphoteric surfactants at concentrations of 1 to 20% by weight, preferably 3 to 8% by weight, based in each case on the total weight of the preparation.
- Use according to Claim 1, characterized in that said preparations comprise cationic polymers at concentrations of 0.01 to 2% by weight, preferably 0.05 to 1.5% by weight, particularly preferably 0.1 to 1% by weight, based in each case on the total weight of the preparation.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102010055768A DE102010055768A1 (en) | 2010-12-23 | 2010-12-23 | Drug combinations of glucosylglycerides and one or more preservatives |
PCT/EP2011/071138 WO2012084410A2 (en) | 2010-12-23 | 2011-11-28 | Active ingredient combinations of glyceryl glucosides and one or more preservatives |
Publications (2)
Publication Number | Publication Date |
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EP2654699A2 EP2654699A2 (en) | 2013-10-30 |
EP2654699B1 true EP2654699B1 (en) | 2018-05-09 |
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EP11788170.6A Not-in-force EP2654699B1 (en) | 2010-12-23 | 2011-11-28 | Active ingredient combinations of glyceryl glucosides and one or more preservatives |
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US (1) | US20140005131A1 (en) |
EP (1) | EP2654699B1 (en) |
DE (1) | DE102010055768A1 (en) |
WO (1) | WO2012084410A2 (en) |
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CN104105472A (en) | 2011-12-20 | 2014-10-15 | 维奥姆生物科学有限公司 | Topical oil composition for the treatment of fungal infections |
DE102012219641A1 (en) * | 2012-10-26 | 2014-04-30 | Beiersdorf Ag | Two-phase product |
DE102016000277A1 (en) * | 2016-01-15 | 2017-07-20 | Beiersdorf Ag | Cosmetic preparations containing benzethonium chloride and diols |
WO2019126703A1 (en) | 2017-12-22 | 2019-06-27 | Ecolab Usa Inc. | Antimicrobial compositions with enhanced efficacy |
IT202100031967A1 (en) * | 2021-12-21 | 2023-06-21 | Beauty & Business S P A | COMPOSITIONS FOR HAIR DYEING IN GEL OR GEL-EMULSION FORM |
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DE19540749A1 (en) * | 1995-11-02 | 1997-05-07 | Beiersdorf Ag | Cosmetic preparations with an effective content of glycosylglycerides |
DE19728900A1 (en) * | 1997-07-07 | 1999-01-14 | Henkel Kgaa | Novel hydrophilic glycosides useful as biodegradable emulsifiers |
FR2825618B1 (en) * | 2001-06-07 | 2008-01-18 | Oreal | USE OF A POLAR ADDITIVE IN A COSMETIC COMPOSITION COMPRISING A LIQUID FATTY PHASE STRUCTURED BY AT LEAST ONE ORGANOGELER TO GIVE THE COMPOSITION A THIXOTROPIC CHARACTER |
FR2839447B1 (en) * | 2002-05-07 | 2007-05-04 | Seppic Sa | NOVEL COMPOSITIONS FOR CUTANE USE BASED ON POLYOLS-GLYCOSIDES |
JP2007500735A (en) * | 2003-05-15 | 2007-01-18 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Hair coloring method comprising reaction of capped diazonium compound with hair, and related compositions and compounds |
DE102005023639A1 (en) * | 2005-05-19 | 2006-11-23 | Beiersdorf Ag | Active substance combination, useful for skin moisturizing and for stabilizing skin barrier, comprises glucosylglycerides, boundary surface-active glucose derivatives and boundary surface-active oligoglycerine derivatives |
US20080220031A1 (en) * | 2005-07-25 | 2008-09-11 | Basf Aktiengesellschaft | Dermocosmetic Preparations |
WO2007128744A2 (en) * | 2006-05-08 | 2007-11-15 | Ciba Holding Inc. | Triazine derivatives |
JP4817182B2 (en) * | 2006-07-20 | 2011-11-16 | 花王株式会社 | Hair cosmetics |
DE102006055041A1 (en) * | 2006-11-17 | 2008-05-21 | Beiersdorf Ag | Cosmetic formulation with glucosylglycerides and cationic emulsifiers |
DE102006055043A1 (en) * | 2006-11-17 | 2008-05-21 | Beiersdorf Ag | Cosmetic formulation with glucosylglycerides and skin brighteners |
DE102006055045A1 (en) * | 2006-11-17 | 2008-05-21 | Beiersdorf Ag | Use of one or more glucosyl glyceride e.g. to prepare a cosmetic preparation to treat or prophylaxis of cellulite, and as a protective skin cream, day or night cream, makeup products, and skin and/or hair caring agent |
DE102006055046A1 (en) * | 2006-11-17 | 2008-05-21 | Beiersdorf Ag | Cosmetic formulation with glucosylglycerides and powder raw materials |
DE102007045241A1 (en) * | 2007-04-20 | 2008-10-23 | Beiersdorf Ag | Cosmetic preparation, useful as an agent that is effective against e.g. gram negative and gram positive bacteria, yeast and/or fungus, comprises piroctone olamine and stabilizing agent e.g. benzaldehyde and/or alkane-diol |
US20090137497A1 (en) * | 2007-11-23 | 2009-05-28 | Beiersdorf Ag | Active ingredient combinations of glucosyl glycerides and creatine and/or creatinine |
EP2234480B1 (en) * | 2008-01-25 | 2013-09-18 | Rhodia Opérations | Liquid preservative compositions comprising glyceryl caprylate and 2-methyl-4-isothiazolin-3-one |
DE102008053549A1 (en) * | 2008-10-28 | 2010-04-29 | Bitop Ag | Glucosylglycerol containing composition |
US20100152480A1 (en) * | 2008-12-16 | 2010-06-17 | Ghare Vishwas Sadhu | Process for synthesis of cationic surfactants |
DE102010013275A1 (en) * | 2010-03-29 | 2011-09-29 | Beiersdorf Ag | Microbiologically stable, application-friendly W / O preparations |
DE102010013277A1 (en) * | 2010-03-29 | 2011-09-29 | Beiersdorf Ag | Microbiologically stable application-friendly preparation with degradation-susceptible active ingredients |
DE102010013274A1 (en) * | 2010-03-29 | 2011-11-17 | Beiersdorf Ag | Microbiologically stable, application-friendly preparations |
-
2010
- 2010-12-23 DE DE102010055768A patent/DE102010055768A1/en not_active Withdrawn
-
2011
- 2011-11-28 EP EP11788170.6A patent/EP2654699B1/en not_active Not-in-force
- 2011-11-28 WO PCT/EP2011/071138 patent/WO2012084410A2/en active Application Filing
- 2011-11-28 US US13/996,630 patent/US20140005131A1/en not_active Abandoned
Non-Patent Citations (1)
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WO2012084410A2 (en) | 2012-06-28 |
US20140005131A1 (en) | 2014-01-02 |
EP2654699A2 (en) | 2013-10-30 |
WO2012084410A3 (en) | 2013-06-20 |
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